Ethyl isocyanate → (11beta,16beta)-21-(Acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamate

HRID 14374노트

반응식

HRID 14374 반응식
[C:1]([O:4][CH2:5][C:6](=[O:35])[C@:7]1([OH:34])[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21]([F:31])([C@@H:22]([O:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:32])[CH:17]=[CH:18]2)[CH2:13][CH2:12]3)[CH2:9][C@@H:8]1[CH3:33])(=[O:3])[CH3:2].[CH2:36]([N:38]=[C:39]=[O:40])[CH3:37].COC(C)(C)C.CCCCCC.C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH2:36]([NH:38][C:39](=[O:40])[O:34][C@:7]1([C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21]([F:31])([C@@H:22]([O:26][Si:27]([CH3:28])([CH3:30])[CH3:29])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:32])[CH:17]=[CH:18]2)[CH2:13][CH2:12]3)[CH2:9][C@@H:8]1[CH3:33])[C:6](=[O:35])[CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH3:37]

참가 물질

5

반응물 3

HCID 8022Ethyl isocyanateHCID 11352672(11beta,16beta)-9-Fluoro-17-hydroxy-16-methyl-3,20-dioxo-11-[(trimethyl-silyl)oxy]-pregna-1,4-dien-21-yl acetateHCID 131728161t-Butyl methyl ether hexane chloroform

생성물 1

HCID 68717367(11beta,16beta)-21-(Acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamate수율 62.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a mixture of (11β,16β)-9-fluoro-17-hydroxy-16-methyl-3,20-dioxo-11-[(trimethyl-silyl)oxy]-pregna-1,4-dien-21-yl acetate (3.11 g, 6.15 mmol) in 41 mL of toluene was added neat ethyl isocyanate (20.5 mL, 259 mmol) and the mixture was refluxed for 48 hours. The resulting solution was cooled to room temperature and evaporated under vacuum to leave a slightly gummy solid. Flash chromatography through a 1 kg column of silica gel eluting with t-butyl methyl ether/hexane/chloroform (1:1:1) gave 2.22 g of the title compound as a white solid.

후처리

  1. temperaturethe mixture was refluxed for 48 hours
  2. customevaporated under vacuum
  3. customto leave a slightly gummy solid

출처 및 근거

ORD 기록
ord-a6663e1989114dada27ab5d109dc064c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732432B2

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